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Received today — 26 April 2025

These former six-figure earners got trapped in jobs because of luxury ‘lifestyle creep’—they sacrificed it all and went in search of financial freedom

26 April 2025 at 09:00
  • These high earners rethought their careers as "lifestyle creep"—where spending rises with income—left them under financial pressure despite impressive paychecks, especially in the face of inflation and social pressure. Sources told Fortune they walked away from lucrative careers to pursue more meaningful, lower-paying paths that prioritize fulfillment, health, and personal values over material success.

Everyone remembers their first paycheck. Whether it's cash-in-hand for a paper round or a significant slip, few people forget the world of potential that opens up once you start earning.

Then people get older and their earnings potential and financial priorities shift: They find themselves with a pet, a mortgage, car payments, a child. Maybe they get promoted: They buy a bigger house, a newer car, holidays for the family are put on a credit card.

Suddenly, a salary that once would have made them feel rich barely scratches the surface.

This is 'lifestyle creep:' When a person's spending ties them into an income bracket.

In a tight housing market, relatively higher interest rate environment and tariff-induced inflation increases on the horizon, even those on the upper end of the income scale are being backed into a corner by their outgoings.

Sources told Fortune why they gave up their high-end homes, C-suite titles, and generous pay packages for careers that truly fulfilled them. But in a world of keeping up with every Jones on social media, it's only getting easier to fall into the same trap.

Money vs meaning

As the former CEO of a New York City-based investment firm, Neal Shah begrudgingly collected the hallmarks of success: The right watch, the correct suit, the $1,000 shoes.

Moving up the ranks from an investment analyst, to hedge fund partner by 27, to leading his own organisation with $20 million in assets under management [AUM] by 31, Shah saw his income soar accordingly.

"At some point in my late 20s I wanted a different life ... but every year it kept getting deferred—it was like golden handcuffs," Shah recalled. "I don't really care for fancy things, but by being in these careers, you're sometimes forced to do things.

"Early in investment banking, I learned the type of suit you wear and the type of tie [matters]—like I was good at my job, but all my bosses told me: 'You need to buy this and dress like this.'

"It's just a perception thing. All the community wears Ferragamo shoes, even though it gave me heartburn to spend that kind of money."

But when Shah's wife was diagnosed with cancer, the decision to leave the finance world could no longer wait.

Crestfallen with the care service available for his wife while he attempted to continue working, Shah became a caregiver full time and the couple moved home to North Carolina—where they encountered other families who had found the same.

In 2021, Shah launched CareYaya Health, which connects universities and their medical students with families in need of support. Now, with more than 30 universities, such as Duke, Harvard, Stanford, and UC Berkley, verifying 28,000 students on the platform, Shah is charging no fees to connect caregivers to families and is not drawing a salary from the business.

"I'm very pleased with my life. Financially, things might have looked different ... and I'd have had a fancy life, but that isn't what drives me, so to some degree it would have been more meaningless," Shah added.

"There's a fulfillment aspect beyond money, which is that all these families that are struggling with care, you're helping. You're motivating these young people to do positive things in their community—that has tremendous value that you can't measure."

It's only getting worse in 2025

Judi Leahy, vice president of Citi's personal wealth management unit, said that even clients with "significant means" will turn to their wealth advisors for help cutting lifestyle costs in 2025.

"People do get caught up in the process of: You have money, but you're not forward thinking," Leahy told Fortune. "My mantra is when in doubt, do without.

"You can't sacrifice all the time ... if you are making money and you have that discretionary income then it's ok to go out and do something for yourself, but it shouldn't be part of your routine spending."

Lifestyle creep is only becoming more of a problem because of social media, easier access to goods and services and societal pressure, added Leahy, adding the problem is compounded in 2025 because of inflation.

"The biggest indication of that is just going grocery shopping," Leahy said. "When you think about your basic needs and your wants, when you go to the grocery store, it's very easy to splurge on things that you don't need really, and the prices have just really gotten out of whack.

"That's one place where you can be completely trapped because you're used to buying certain things and those prices have gone exponentially higher and you're still in the same game."

Take even the most basic purchase of a dozen large eggs. According to the St Louis Fed, the cost of eggs continues to spike, sitting at more than $6 in March 2025 compared to $2.99 a year prior.

Anyone worried about their spending vs. their necessary income needs to compile a brutally honest financial plan, Leahy added. "Use the different scenarios: If you retire at 60, if you retire at 65, if you take Social Security, if we sell the main house and buy a smaller house—what does that look like?"

"All of that should get factored in, and you have a very sobering moment to say 'I can make it' or 'Oh my god, you better go get a second job.' Once you have everything in black and white, things become more real."

Stepping away from it all

Unlike many in his family, Gene Cabalerro didn't grow up with an entrepreneurial itch, so he spent a happy decade in Nashville working at Dell Technologies.

His days consisted of hard work, enjoying his $3,000-a-month apartment in the best building in town, regular sports tickets at the nearby Nissan stadium, and weekends partying.

On a Friday afternoon a few years ago, looking out over commercial parking lots around his office, Cabalerro considered his lifestyle creep for the first time. He was counting the speedboats parked in the nearby lots, towed to work ahead of a weekend on the water.

"It was a fun place to live, a great environment, and you're surrounded by wonderful people that are also doing well. You just wanna keep up with them and keep striving," Cabalerro recounted.

But then an opportunity to invest in and lead GreenPal—an on-demand lawn care platform—was offered and the entrepreneurial itch kicked in.

"I'm now living in my sister's spare bedroom, and last year I stayed 196 nights in Marriotts across the world," Cabalerro said. "I'm in Peru right now, and I've already got six trips planned this year. Life is great, it just takes those shitty few first years."

The story is the same for Christopher Kaufman, who left behind his $1.5 million California home, healthy 401k, and high-end hotel stays to complete a doctorate and lecture at universities.

Kaufman went in search of more independence than his six-figure role in tech afforded him, but the decision to leave his job was made all the more complex by the medical insurance it provided him and his wife, who suffers with autoimmune issues.

"There were moments of regret," he recalls, particularly when the couple were searching for insurance cover.

Now living in the Coachella Valley, Kaufman added: "Tears were shed, going: How much do we burn into our retirement? Luckily, we didn't have to do that, but we got right up to the edge of saying: 'We could burn down what we built up' and that was not part of the plan.

"From teaching, I'm now probably earning between 5% and 10% of what I was. I'm ten times happier, but I'm making ten times less money."

This story was originally featured on Fortune.com

Lifestyle creep is only going to get easier in an inflationary environment, warned one personal finance expert.
Received before yesterday

Nearly five years after Tony Hsieh died in a house fire, it looks like the Zappos CEO’s will has finally been found

24 April 2025 at 14:40
  • Tony Hsieh left behind hundreds of millions of dollars after his accidental death caused by a house fire in 2020. But after years of his family, friends, and colleagues battling over his fortune in court, it looks like an original will, signed by Hsieh and five witnesses in 2015, has been discovered.

Tony Hsieh, cofounder and CEO of the shoe and clothing retailer Zappos, died in a house fire in New London, Conn., in 2020. While he struggled with substance abuse, medical examiners ruled his death an accident. Hsieh was just 46 years old. 

Since then, Hsieh’s inner circle has spent years fighting in court over his estate, which was worth hundreds of millions of dollars. Most of his fortune came from Hsieh’s 2009 sale of Zappos to Amazon for $1.2 billion, and Hsieh had apparently left sticky notes all over his Park City, Utah, home, promising millions to friends and former colleagues.

But in a surprise twist, it seems as though an original will—signed by Hsieh and five witnesses, dated March 13, 2015—has been discovered.

According to a filing from the Clark Country District Court in Nevada, the document was found in February in the personal belongings of a man who suffered from Alzheimer’s disease, named Pir Muhammad. It’s not clear how Muhammad and Hsieh knew each other, but the court filing says Muhammad (who did not know Hsieh had died) was given “exclusive possession” of the original will to prevent any tampering. Muhammad was also one of the five witnesses who signed the will; another witness, named Ishrat Daud, told the Wall Street Journal he indeed acted as a witness “a number of years ago” but had nothing more to say on the matter.

The recent court filing also mentioned a video recording was made, but it’s unclear if the video was also found, and what’s even featured on the video. The next scheduled hearing for this case, on May 22, may shed more light on the matter.

As for the will itself, Hsieh left $3 million to Harvard University, his alma mater; $500,000 each to Unicef and the American Red Cross; $250,000 each to the Buffett Foundation, Americares Foundation, and the Gates Foundation; $1 million to his trustee, Muzammal Hussain, and STRYV365, a nonprofit dedicated to helping young people navigate and deal with trauma; and $500,000 each to his mother, Judy, father Richard, and brothers Andrew and David.

The will also reportedly includes a no-contest clause that says if any of his four remaining family members fight Hsieh’s wishes, none of them will receive any of his gifts.

“I have structured my way of surprising and leaving essentially all my beneficiaries to experience the ‘WOW’ factor in their life,” the purported will says. “I want my beneficiaries to ‘live in the wow.’”

This story was originally featured on Fortune.com

© David Paul Morris—Bloomberg/Getty Images

Tony Hsieh, then CEO of Zappos, in Las Vegas, May 18, 2017.

I helped my daughter get into law school by pulling strings and got her a job at my law firm. Some colleagues don't respect her at work.

13 April 2025 at 12:47
a man hovering over a woman at her work desk
The author (not pictured) helped his daughter jump-start her law career.

MTStock Studio/Getty Images

  • When my daughter needed to get into law school, I pulled strings to get her accepted.
  • I also got her a job at my law firm after graduation, and now some colleagues don't respect her.
  • I sometimes wonder if I made the right decision, but I don't regret helping her.

One of my fondest memories of my daughter is going home after a long day of work at my old law firm and seeing her sitting on the steps, anxiously waiting to ask me about my day. She would run toward me, grab my briefcase, and help me into the house.

She would then call me Superman and ask if I had settled any big cases or saved the world that day. I was a paralegal at the time, working my way up the totem pole, but the idea of helping others through legal processes excited her. That's when I knew that she would make a great lawyer.

True to that, her passion for law never wavered. While many kids are fickle and change their minds about careers as they go through life, my daughter was consistent in what she wanted.

Eventually, I earned my law degree and became a practicing lawyer. She enjoyed helping in my office during spring and summer break. As a parent, watching her in action inspired my desire to set her up for success.

I helped my daughter out early in her career

Having attended law school, I knew a couple of school administrators and professors who equally encouraged my daughter to enroll in a legal course since she wanted to practice law.

My relationship with them played a great role in helping her secure a spot in a good school, but she still had to do the work and keep her grades up to graduate.

After graduation, I vouched for her skills and expertise among the other lawyers in my firm. Most people saw it as a father speaking highly of her daughter. Because of the great history we had and the standard employment protocol, the legal experts put her through a round of interviews, which she aced.

I saw nothing wrong with using my connections to help my daughter land a job. She is smart, graduated with honors, and passed the bar exam. Some people believe that we should all start from the bottom up, but I've always been the kind of person who would never turn down an added advantage.

My daughter isn't well-respected at work by some

I've worked for over 30 years in my law firm. It's no secret that I used my influence and the relationships I have formed to help my daughter acquire a job. I don't shy away from pointing this out to colleagues. I even discussed my desires and intentions with them while my daughter was still in school.

However, the downside is that some colleagues think my daughter didn't earn her keep. It feels like she is not well-respected for her brilliant mind and always gets the shorter end of the stick when it comes to work projects.

This has played out in numerous instances, and she even feels like she has to downplay her ideas so the limelight is not constantly on her. Granted, she could find a job solely based on her accomplishments, but as a parent, I don't see the purpose of going the long way when I can help.

I've had moments where I wonder if I did the right thing, but watching her come to work every day with a smile on her face despite the odds makes me feel like we are on the right path.

I've had numerous conversations with her about some of her colleagues feeling like she got the easy way out. This would be disheartening for anyone, but it only fuels her fire to do better and chart her own career path.

She knows she can leave and find a job in any other law firm of her choosing, but working together offers us both a sense of comfort that we are holding on to.

I don't regret helping my daughter

I'm slowly realizing that a job connection for any of my children could leave them feeling like they constantly need to prove themselves among their colleagues.

I encourage all of them to be their best. I've imparted life lessons and resources to see them through any situation. But if my daughter ever feels like my influence is standing in her way, I would gladly step back and let her find her own path.

As we've heard, there's no manual to parenting. Sometimes, we make decisions we think are in the best interest of our children's happiness, only to deal with unexpected challenges down the line.

Read the original article on Business Insider

I kept getting skipped over for a promotion. Once I moved my desk to a more visible spot in the office, my career took off.

4 April 2025 at 11:07
a woman sitting at her work desk with two screen in front of her
The author (not pictured) moved her desk in the office and got promoted.

Pancake Pictures/Getty Images/Image Source

  • I thought hard work would earn me a promotion.
  • However, I was continuously skipped over for promotions and larger projects at my design firm.
  • A colleague told me to move my desk to be more visible in the office, and I instantly got more work.

Growing up, I was always taught that hard work pays off, so I assumed that was how the real world worked.

I worked hard in high school, earning all A's and just one B in my last semester. I got into my first choice school for college and landed every job interview up to that point. My hard work paid off.

One of my college professors then recommended me to the hiring manager for a paid internship at a design firm in Chicago while I was still in school. She had noticed my excellent work and active participation in her class.

Upon graduation, I was hired full-time at that architecture and design firm to work in the resource library. I planned to climb the ladder and land a role on the design team with the hard-work mentality that had served me well thus far.

I figured if I kept exceeding expectations, I'd be noticed and promoted. But it wasn't that easy, and one piece of career advice changed everything for me.

I kept getting passed over for a promotion

I gave my all to the role and the firm. However, I was continually passed over for larger projects and for promotions.

I kept going above and beyond, working 12- to 14-hour days to complete my duties and assisting the design teams on their projects. Yet, I still wasn't selected for a promotion outside the library.

When I asked around why I hadn't been picked for an associate position, several people thought I already was one because of all my work and accomplishments, so no one thought to nominate me. Designers I had spoken to said I hadn't done anything wrong; I just simply wasn't there in the team area when assignments were made.

Finally, an architectural principal saw me working late one evening and asked what my goal with the firm was. I told him I wanted to move out of the resource library and onto design projects full-time.

He shrugged and said three words that changed the trajectory of my career: "Move your desk."

He finally explained that people assign projects to people that are top of mind. Since I was tucked away in a remote corner of the office, I was rarely considered. I needed to move my desk to the exact area where I'd like to work so they could literally see my face.

At the time, I was an avid rule follower, so I was afraid to move my work desk without being invited, but I did it anyway.

I took my colleague's advice, and everything changed

I moved my desk to the office's main area — where I had wanted to work — and did my library work from there. Being physically present in the new workspace, I was assigned to projects I wanted to be on almost overnight.

I worked on hotels local to Michigan Ave and overseas. I was also handed a multimillion-dollar military project, for which I even got to travel.

I was getting assignments time and time again — both in the hospitality and military sectors.

Finally, I was promoted to junior designer — just a few weeks after moving my desk.

Hard work isn't always the answer

After my experience at the design firm, I learned one crucial lesson: Hard work alone isn't what gets you places. It's how you play the game; it's proactively putting yourself in places and positions you want to be in — before you're actually "there."

Unfortunately, I spent many late nights in the wrong place in the office, where no one could see my accomplishments.

My performance and results are always stellar, but I've learned I can be great without running myself into the ground.

As long as I put myself in front of people with power, I can take my career to the next level.

Read the original article on Business Insider

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